US4088679A - Process for the preparation of perpropionic acid solutions - Google Patents
Process for the preparation of perpropionic acid solutions Download PDFInfo
- Publication number
- US4088679A US4088679A US05/678,820 US67882076A US4088679A US 4088679 A US4088679 A US 4088679A US 67882076 A US67882076 A US 67882076A US 4088679 A US4088679 A US 4088679A
- Authority
- US
- United States
- Prior art keywords
- hydrogen peroxide
- acid
- propionic acid
- reaction
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/24—Peroxy compounds the —O—O— group being bound between a >C=O group and hydrogen, i.e. peroxy acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
Definitions
- the present invention relates to a process for the preparation of perpropionic acid from hydrogen peroxide and propionic acid.
- perpropionic acid from hydrogen peroxide and propionic acid is known (Swern, Organic Feroxides I, Wiley, 1970, page 369-372).
- the reaction of hydrogen peroxide with propionic acid takes place in the presence of an acid catalyst according to equation (1) ##STR1## to give an equilibrium mixture which contains perpropionic acid, propionic acid, hydrogen peroxide, water and the acid catalyst.
- concentration of perpropionic acid depends on the concentrations of the feed materials and on the molar ratio of hydrogen peroxide and propionic acid in the feed. In general, hydrogen peroxide is used in concentrations of from 30 to 90% by weight, preferably 50 to 70% by weight.
- Propionic acid is preferably employed in the pure form or as an aqueous solution.
- Suitable acid catalysts are the mineral acids, for example sulphuric acid, acid salts, such as, for example, sodium bisulphate, or cation exchangers based on sulphonated, partially crosslinked polystyrenes in the H + ion form.
- the amount of these catalysts can vary within wide limits.
- the mixtures formed according to equation (1) can be used in a known manner for oxidation reactions.
- perpropionic acid can be prepared by reaction of hydrogen peroxide with propionic acid in the presence of an acid, preferably sulphuric acid, under explosion-proof conditions when the reaction is carried out using a molar ratio of hydrogen peroxide:propionic acid employed of more than 3.5:1, the reaction temperature is restricted to a maximum of 60° C and the ratio of hydrogen peroxide (100% by weight):water by weight before the start of the reaction with propionic acid is restricted to a maximum of about 0.8, the sulphuric acid concentration in the reaction mixture being 10-40% by weight.
- an acid preferably sulphuric acid
- reaction mixtures such as are formed according to equation (1) are explosion-proof when the molar ratio of hydrogen peroxide:propionic acid employed is restricted to more than 3.5:1, preferably 3.8-10:1, the reaction temperature is restricted to a maximum of 60° C and the ratio of hydrogen peroxide (100% by weight): water by weight before the start of the reaction with propionic acid is restricted to a maximum of about 0.8.
- sulphuric acid is used as catalyst, its concentration in the reaction mixture is preferably 10-40% by weight.
- the reaction temperature in the preparation of the reaction mixtures is generally between 20° and 60° C, preferably 30°-45° C and preferentially 35°-40° C.
- the present invention is illustrated by the tests which follow and the term explosion hazard, which is used there, is also explained.
- a method for determining the sensitivity of explosive materials towards exposure to heat is to heat the materials in a steel bomb which is closed off by a nozzle plate with a well-defined orifice.
- the steel bomb is fabricated from deep-drawing sheet metal and has an internal diameter of 24 mm, a length of 75 mm and a well thickness of 0.5 mm. At its open end, the bomb is provided with a collar.
- the bomb is closed by a circular nozzle plate provided with a bore. Nozzle plates having the following diameters for the cylindrical outlet orifice for the gases produced by the decomposition are used: 1; 1.5; 2; 2.5; 3; 3.5; 4; 4.5; 6; 8; 10; 12; 14; 16 and 20 mm.
- the materials to be investigated are introduced into the steel bomb and, in order to prevent the initiation of a catalytic decomposition, the walls of the steel bomb can be provided with a coating of polyethylene or the like.
- the volume of the material sample is about 27 ml.
- the samples are exposed to heat by supplying heat in an amount of, on average, 2.4 koals/sec. from 4 Teclu burners. With 3 tests, at least one explosion must take place, the bomb being split into 3 or more parts ("limiting diameter").
- the limiting diameter determined in this way is to be regarded as a measure of the heat sensitivity of the material examined. The higher the limiting diameter, the higher is the heat sensitivity. Values of 2-2.5 mm are to be regarded as transition values into the dangerous range, values in excess of 2.5 mm indicating that the reaction mixture is dangerously heat sensitive.
- reaction mixtures investigated were prepared from hydrogen peroxide of the indicated concentration using anhydrous propionic acid and concentrated sulphuric acid.
- the results of the steel bomb tests are given in the table which follows.
- the examples indicate as an appropriate limit for the ratio of hydrogen peroxide:water at the start of the reaction, 0.8, which of course includes 0.82.
- 0.8 which of course includes 0.82.
- a lower limit that ratio can be 0.10; a preferred range is 0.30 to 0.60.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2519300A DE2519300C3 (de) | 1975-04-30 | 1975-04-30 | Verfahren zur Herstellung von Perpropionsäurelösungen unter explosionssicheren Bedingungen |
DT2519300 | 1975-04-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
US4088679A true US4088679A (en) | 1978-05-09 |
Family
ID=5945453
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/678,820 Expired - Lifetime US4088679A (en) | 1975-04-30 | 1976-04-28 | Process for the preparation of perpropionic acid solutions |
Country Status (25)
Country | Link |
---|---|
US (1) | US4088679A (pt) |
JP (1) | JPS51133225A (pt) |
AR (1) | AR212705A1 (pt) |
AT (1) | AT344676B (pt) |
BE (1) | BE841210A (pt) |
BG (1) | BG27364A3 (pt) |
BR (1) | BR7602597A (pt) |
CA (1) | CA1058212A (pt) |
CH (1) | CH601223A5 (pt) |
CS (1) | CS189766B2 (pt) |
DD (1) | DD125929A5 (pt) |
DE (1) | DE2519300C3 (pt) |
ES (1) | ES447412A1 (pt) |
FI (1) | FI761182A (pt) |
FR (1) | FR2309532A1 (pt) |
GB (1) | GB1518008A (pt) |
IE (1) | IE42802B1 (pt) |
IL (1) | IL49485A (pt) |
IT (1) | IT1061689B (pt) |
NL (1) | NL7604533A (pt) |
NO (1) | NO142121C (pt) |
PL (1) | PL98406B1 (pt) |
RO (1) | RO74966A (pt) |
SE (1) | SE418081B (pt) |
ZA (1) | ZA7602527D (pt) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4297298A (en) * | 1979-08-01 | 1981-10-27 | L'air Liquide, Societe Anonyme Pour L'etude Procedes Georges Claude | Method of preparing stable dilute solutions of aliphatic carboxylic peracids, and the resulting solutions |
WO2017155441A1 (en) * | 2016-03-09 | 2017-09-14 | Perstorp Ab | Production equipment for production of caprolactone |
WO2017155442A1 (en) * | 2016-03-09 | 2017-09-14 | Perstorp Ab | Production equipment for production of a caprolactone |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05100648A (ja) * | 1991-10-04 | 1993-04-23 | Mitsubishi Electric Corp | テストパターン発生装置 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA735489A (en) * | 1966-05-31 | Weiberg Otto | Process of producing solutions of pure aliphatic percarboxylic acids | |
CA744391A (en) * | 1966-10-11 | J. Wenzke Carroll | Method of producing peracids |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL267716A (pt) * | 1960-08-06 | |||
FR1352479A (fr) * | 1962-04-04 | 1964-02-14 | Fmc Corp | Procédé de production de peracides aliphatiques inférieurs |
-
1975
- 1975-04-30 DE DE2519300A patent/DE2519300C3/de not_active Expired
-
1976
- 1976-04-28 IE IE894/76A patent/IE42802B1/en unknown
- 1976-04-28 CS CS762789A patent/CS189766B2/cs unknown
- 1976-04-28 FI FI761182A patent/FI761182A/fi not_active Application Discontinuation
- 1976-04-28 US US05/678,820 patent/US4088679A/en not_active Expired - Lifetime
- 1976-04-28 FR FR7612613A patent/FR2309532A1/fr active Granted
- 1976-04-28 AR AR263147A patent/AR212705A1/es active
- 1976-04-28 IL IL49485A patent/IL49485A/xx unknown
- 1976-04-28 CH CH536176A patent/CH601223A5/xx not_active IP Right Cessation
- 1976-04-28 CA CA251,292A patent/CA1058212A/en not_active Expired
- 1976-04-28 PL PL1976189123A patent/PL98406B1/pl unknown
- 1976-04-28 GB GB17183/76A patent/GB1518008A/en not_active Expired
- 1976-04-28 AT AT311076A patent/AT344676B/de not_active IP Right Cessation
- 1976-04-28 NO NO761474A patent/NO142121C/no unknown
- 1976-04-28 SE SE7604888A patent/SE418081B/xx not_active IP Right Cessation
- 1976-04-28 BG BG7633052A patent/BG27364A3/xx unknown
- 1976-04-28 JP JP51047905A patent/JPS51133225A/ja active Granted
- 1976-04-28 IT IT49231/76A patent/IT1061689B/it active
- 1976-04-28 DD DD192571A patent/DD125929A5/xx unknown
- 1976-04-28 BR BR2597/76A patent/BR7602597A/pt unknown
- 1976-04-28 ES ES447412A patent/ES447412A1/es not_active Expired
- 1976-04-28 NL NL7604533A patent/NL7604533A/xx not_active Application Discontinuation
- 1976-04-28 RO RO7685936A patent/RO74966A/ro unknown
- 1976-04-28 ZA ZA19762527D patent/ZA7602527D/xx unknown
- 1976-04-28 BE BE2054993A patent/BE841210A/xx not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA735489A (en) * | 1966-05-31 | Weiberg Otto | Process of producing solutions of pure aliphatic percarboxylic acids | |
CA744391A (en) * | 1966-10-11 | J. Wenzke Carroll | Method of producing peracids |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4297298A (en) * | 1979-08-01 | 1981-10-27 | L'air Liquide, Societe Anonyme Pour L'etude Procedes Georges Claude | Method of preparing stable dilute solutions of aliphatic carboxylic peracids, and the resulting solutions |
WO2017155441A1 (en) * | 2016-03-09 | 2017-09-14 | Perstorp Ab | Production equipment for production of caprolactone |
WO2017155442A1 (en) * | 2016-03-09 | 2017-09-14 | Perstorp Ab | Production equipment for production of a caprolactone |
EP3426646A4 (en) * | 2016-03-09 | 2019-09-04 | Ingevity UK Ltd | PRODUCTION EQUIPMENT FOR THE PRODUCTION OF A CAPROLACTONE |
Also Published As
Publication number | Publication date |
---|---|
FI761182A (pt) | 1976-10-31 |
BG27364A3 (en) | 1979-10-12 |
IE42802B1 (en) | 1980-10-22 |
AT344676B (de) | 1978-08-10 |
JPS5753784B2 (pt) | 1982-11-15 |
SE418081B (sv) | 1981-05-04 |
JPS51133225A (en) | 1976-11-18 |
NO761474L (pt) | 1976-11-02 |
PL98406B1 (pl) | 1978-05-31 |
IE42802L (en) | 1976-10-30 |
BE841210A (fr) | 1976-10-28 |
NO142121C (no) | 1980-07-02 |
AU1341776A (en) | 1977-11-03 |
GB1518008A (en) | 1978-07-19 |
DE2519300B2 (de) | 1978-10-19 |
NL7604533A (nl) | 1976-11-02 |
DE2519300A1 (de) | 1976-11-11 |
CH601223A5 (pt) | 1978-06-30 |
DE2519300C3 (de) | 1979-06-13 |
IL49485A0 (en) | 1976-06-30 |
RO74966A (ro) | 1982-09-09 |
AR212705A1 (es) | 1978-09-15 |
CA1058212A (en) | 1979-07-10 |
FR2309532B1 (pt) | 1981-04-30 |
FR2309532A1 (fr) | 1976-11-26 |
IL49485A (en) | 1978-12-17 |
CS189766B2 (en) | 1979-04-30 |
IT1061689B (it) | 1983-04-30 |
BR7602597A (pt) | 1976-11-23 |
SE7604888L (sv) | 1976-10-31 |
ZA7602527D (en) | 1977-04-27 |
ES447412A1 (es) | 1977-07-01 |
ATA311076A (de) | 1977-12-15 |
NO142121B (no) | 1980-03-24 |
DD125929A5 (pt) | 1977-06-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4088679A (en) | Process for the preparation of perpropionic acid solutions | |
US4087454A (en) | Process for the preparation of perpropionic acid solutions | |
US4059619A (en) | Process for the preparation of percarboxylic acid solutions | |
US3236883A (en) | Process for the manufacture of peracids | |
KR100289593B1 (ko) | 디니트로톨루엔의 제조방법 | |
US6641791B2 (en) | Generation of boron-trifluoride and sulphuric acid from boron trifluoride hydrate | |
SU858562A3 (ru) | Способ получени водных растворов надпропионовой кислоты | |
US5449835A (en) | Synthesis of bis(2,2-dinitropropyl) formal (BDNPF) | |
US4192812A (en) | Oxidation of waxes in the presence of long chain quaternary ammonium and phosphonium compounds | |
US2324248A (en) | Catalytic halo-substitution of saturated organic compounds | |
FI65763B (fi) | Stabiliserade vattenloesningar av vaeteperoxid | |
Walker et al. | The Decomposition of Liquid Hydrocyanic Acid. | |
Gokavi et al. | Kinetics and mechanism of oxidation of aliphatic and aromatic alcohols by in situ generated bromine in reaction between oxone and bromide ion | |
US3179702A (en) | Reaction of carbon dioxide with fluorine | |
SU1495289A1 (ru) | Способ получени гидроксиламинсульфата | |
SU937444A1 (ru) | Способ получени глутаровой кислоты | |
US2464572A (en) | Production of nitroparaffins | |
RU2076094C1 (ru) | Способ получения нитрометана | |
Emeish | Solvent effect on the rate of N (III)/Cl (V) reaction | |
US3428675A (en) | Process for the preparation of oxalic acid | |
IL22217A (en) | Production of hydroxylamine sulphate | |
SU1163256A1 (ru) | Способ определени тетрагидрофталевого ангидрида | |
SU391416A1 (ru) | Способ определения каталитической активности гидратных сульфатных катализаторов | |
Debenham et al. | The thermal decomposition of some organic solids. Part II. m-Nitroperoxybenzoic acid and related peroxyacids | |
RU2109547C1 (ru) | Способ определения устойчивости системы экстрагент - азотная кислота |